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Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Overview

The Wicked St. Augustine tour delves into the unwritten history of the nation's oldest city. You will hear stories of the illicit industries that made the town a financial success, all while avoiding the reputation of a sinful city. From its founding St. Augustine had a thriving tavern, gambling and prostitution industry, even while portraying a city founded on religious principles. See the locations of high stakes gambling, speak easy taverns, and private clubs which skirted around the laws of the day, like prohibition. Learn how the political powers knew of these activities, secretly supported their providers, all while keeping a squeaky clean image.

City: St Augustine

Sat 09 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Sat 09 Nov

Starting at $30.00

Make a reservation

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What's Included

Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'

Additional Info

Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels
Guides required to regularly wash hands

What To Expect

Lightner Museum

The courtyard in front of the old Alcazar Hotel, now the Lightner Museum, also in full view of the old Ponce de Leon Hotel, now Flagler College.

Flagler College

Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.

St. George Street

Here the stories of the private clubs that lined this and the adjoining streets, gambling halls, speak easies, and boarding houses for upscale vacationers, to the working men of the city.

Plaza de la Constitucion

From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).

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Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (38)

Chelsea M

Aug 2022

A highlight of my most recent trip to St. Augustine, this tour was thoroughly enjoyable and educational. The tour guide, Ann, who’s also the author of the book “Wicked St. Augustine,” is a fantastic storyteller who walks you through the city’s REAL history. Speaking of walking, the tour’s route is relatively short, making it easy for most to walk; most of the stops allow for sitting, too. Ann is also accommodating to your group’s needs and is more than happy to answer any questions you may have. I 100% recommend this tour!

Response from Host

Aug 2022

We're so glad you enjoyed the experience. Ann is very passionate about the subject matter and does a great job. Thank you for taking the time to review.

Carolyn12309

Aug 2022

This tour was fantastic! Everyone in my group loved it. The tour guide has done an incredible amount of research on the history of St. Augustine and brought that history life. The stories she told were fascinating. There was no point during our 2+ hours together that anyone in my group felt bored. If we had had more time, we could have listened to the tour guide into the wee hours of the night!

Response from Host

Aug 2022

So glad you enjoyed your experience with Ann, she does a great job of showing a hidden history of our city.

Carolyn_C

Aug 2022

This tour was fantastic! The tour guide has done an incredible amount of research on the history of St. Augustine and brought that history life. The stories she told were fascinating. There was no point during our 2+ hours together that anyone in my group felt bored. If we had had more time, we could have listed to the tour guide into the wee hours of the night!

Response from Host

Aug 2022

So glad you enjoyed the experience. Ann has done an incredible job of researching her tour. We appreciate the time you took to share your review.